Leo and the Cubs: America’s Greatest Losers

Another year, another disappointment for the ever-disappointed Cubs fans, a group of which I am a member by only the loosest standards. The Cubs’ 107-year-long losing streak has become the stuff of baseball legend, and though some are optimistic, I don’t think it’s ending anytime soon. But this perpetual failure is what makes them so endearing; everyone loves an underdog, and who can lay claim to that status more than the Chicago Cubs?

There’s one contender, at least, in the form of Leonardo DiCaprio. The actor has been nominated for an Academy Award no less than four times, and still has yet to win. True, Leo hasn’t lost quite as many times as the Cubs, but his story is arguably more tragic. There have been many years in which the Cubs never had a chance to win, and the team (along with the fans) accepted this early on. But Leo has come this close to the Oscar, close enough to see the golden light bouncing off its head, only to have it denied to him time and time again. Not to mention that when the Cubs lose, they can count on the love and support of their loyal fanbase; when Leo loses, he suffers alone.

It seems that every year brings with it a movie that has “Dicaprio Oscar Bid” written all over it. Watching Leo whisper through The Revenant’s trailer, his face chapped and grimy, you can practically hear him thinking, “This is the one, I can feel it.” But just like the Cubs, Leo would lose something if he ever won. He’d no longer be the Oscars’ underdog, who keeps smiling through the soul crushing disappointment of yet another loss. We’ve all felt that disappointment, and that’s why we’re so drawn to DiCaprio and the Cubs: their failures make them human. They may not bring home the gold, but they’ve got heart, dammit, and that’s what really counts.

So come February, when Leo’s listening to the presenters rattle off the Best Actor nominees, his years-old acceptance speech tucked into his jacket pocket, a part of me will be hoping for another loss. Not out of malice, but rather the hope that he’ll stay my favorite loser.